A Computational Study of Euglobal G1 - An Acylphloroglucinol with Anticancer Activity

Author(s): Liliana Mammino.

Journal Name:Current Bioactive Compounds

Volume 10 , Issue 3 , 2014

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Abstract:

Euglobal G1 (E-G1) is an acylphloroglucinol exhibiting anticancer activity. The phloroglucinol moiety is a derivative of jensenone and forms a chroman skeleton fused to a terpene unit. A computational study of E-G1 was carried out in vacuo at the HF/6-31G(d,p), DFT/B3LYP/6-31+G(d,p) and MP2/HF/6-31G(d,p) levels, and in solution at the DFT/B3LYP/6-31+G(d,p) level, with the PCM model and considering three solvents – chloroform, acetonitrile and water. All the computed molecular properties are reported and analysed in detail. The results in vacuo are compared with those of two other molecular structures, one (E-G2) differing by interchanged positions of the acyl chains with respect to E-G1 and proven non-active against cancer; the other (GX) differing from E-G1 only by the position of the bridge in the terpene unit. It appears reasonable to infer that the nature and positions of the two acyl chains in E-G1 have a role in determining its biological activity.

Keywords: Acylphloroglucinols, anticancer activity, euglobals, hydrogen bonding, polyphenols, solvent effect.

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Article Details

VOLUME: 10
ISSUE: 3
Year: 2014
Page: [163 - 180]
Pages: 18
DOI: 10.2174/157340721003141013142704
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